3-Aminophenol → 1-(3-Hydroxyanilino)-4-(4-pyridylmethyl)phthalazine

HRID 49868Notes

Reaction equation

HRID 49868 reaction equation
Cl[C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[C:5]([CH2:12][C:13]2[CH:18]=[CH:17][N:16]=[CH:15][CH:14]=2)=[N:4][N:3]=1.[NH2:19][C:20]1[CH:21]=[C:22]([OH:26])[CH:23]=[CH:24][CH:25]=1>C([O-])(=O)C.C(=O)([O-])[O-].[K+].[K+].CO>[OH:26][C:22]1[CH:21]=[C:20]([CH:25]=[CH:24][CH:23]=1)[NH:19][C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[C:5]([CH2:12][C:13]2[CH:18]=[CH:17][N:16]=[CH:15][CH:14]=2)=[N:4][N:3]=1

Participants

6

Reactant 2

HCID 115683-AminophenolHCID 19446091-Chloro-4-(4-pyridinylmethyl)phthalazine

Product 1

HCID 64193911-(3-Hydroxyanilino)-4-(4-pyridylmethyl)phthalazine

Reagents, catalysts & solvents 3

HCID 175AcetateSolventHCID 887MethanolSolventHCID 11430Potassium CarbonateSolvent

Conditions

Temperature
120 °C

Procedure

A mixture of 0.384 g (1.5 mmol) 1-chloro-4-(4-pyridylmethyl)phthalazine and 0.491 g (4.5 mmol) 3-aminophenol is heated under nitrogen atmosphere for 1 h at 90° C. and for 3 h at 120° C. The reaction mixture is then taken up in a mixture of 30 ml acetate and 20 ml 20% aqueous potassium carbonate solution while stirring for about 4 h, and the filtration material is digested for 20 min in 20 ml of boiling methanol. After cooling to RT, filtration, washing of the filter residue with methanol, and drying under HV (8 h, 130° C.), title compound is obtained with a water content of 1.94%; m.p. 217-219° C.; ESI-MS: (M+H)+=329.

Workup

  1. temperatureAfter cooling to RT
  2. filtrationfiltration
  3. washwashing of the filter residue with methanol
  4. customdrying under HV (8 h, 130° C.)

Sources & evidence

ORD record
ord-13dac9bc62b74569911d6cec94e6ece0
Source dataset
uspto-grants-2004_03
Patent number
US06710047B2

Reaction notes

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